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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2363475Generated: October 31, 2026

3-(Trifluoromethyl)benzaldehyde → N-[(3aR,4S,6aS)-2-(3-fluorobenzyl)octahydrocyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide

https://huagongshe.com/reaction/2363475

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-(Trifluoromethyl)benzaldehydeHCID 67990—
Reactant2,2-Dicyclohexyl-N-((3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl)acetamideHCID 46213053—
Reactant3-Methyl-N-[(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-yl]-2-phenylbutanamideHCID 66590685—
ProductN-[(3aR,4S,6aS)-2-(3-fluorobenzyl)octahydrocyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamideHCID 46213305—

Reaction Steps

The title compound was prepared by substituting 3-fluorobenzaldehyde for 3-(trifluoromethyl)benzaldehyde and 3-methyl-N-[(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide from Example 83 Step A for 2,2-dicyclohexyl-N-[(3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]acetamide in the procedure described for Example 54: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.61 (t, J=8.0, 1H), 7.64 (dd, J=4.1, 7.0, 2H), 7.37-7.16 (m, 5H), 7.13 (d, J=7.6, 1H), 7.04 (s, 1H), 4.33 (dd, J=5.7, 12.4, 1H), 3.57 (d, J=13.5, 0.5H), 3.48 (d, J=13.4, 0.5H), 3.42 (d, J=13.5, 0.5H), 3.30 (d, J=13.5, 0.5H), 3.23 (d, J=10.5, 1H), 2.90 (dd, J=2.9, 9.1, 0.5H), 2.70-2.61 (m, 1H), 2.59-2.53 (m, 1H), 2.53-2.45 (m, 1H), 2.44-2.31 (m, J=18.5, 1H), 2.27 (t, J=7.7, 1H), 2.19 (dd, J=6.3, 13.0, 1H), 2.12 (dd, J=6.0, 12.3, 0.5H), 1.93-1.80 (m, J=6.9, 12.4, 20.6, 1H), 1.79-1.64 (m, 1H), 1.47-1.24 (m, 2H), 1.20 (dd, J=3.1, 6.4, 3H), 0.70 (d, J=6.7, 3H); MS (ESI+) m/z 395 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08691865B2
Source datasetuspto-grants-2014_04
ORD IDord-1eb9f440967346569a02ac0af13c3ce5
Source noteuspto-grants-2014_04